Mono or disazo dyestuffs containing a diamino,halotriazinyl or pyrimidinyl substituent

ABSTRACT

Valuable reactive dyestuffs containing no acid, salt-forming, water-solubilizing groups and which, among others, can be applied to hydrophobic fibers especially polyamide fibers from organic solvents, especially aprotic solvents correspond to the formula   WHEREIN D represents the radical of an organic dyestuff, Q represents the bridging member -NX3-, -O-, -S- or -NX3CO-, whereby X3 denotes hydrogen or a lower alkyl group, R represents the radical of a nitrogen heterocycle containing at least one substitutent which can be split off as anion and which is bound to a ring carbon atom adjacent to a tertiary nitrogen atom, X1 represents hydrogen, an alkyl or an alkoxyalkyl group and X2 represents an alkyl or an alkoxyalkyl group having in all at least 4 carbon atoms, whereby X1 and X2 must together contain, when X1 denotes an alkyl or an alkoxyalkyl group, at least 8 carbon atoms, or X1 represents a cyclohexyl radical, unsubstituted or substituted by lower alkyl groups having preferably 1 to 4 carbon atoms, and X2 represents an unsubstituted or substituted alkyl group having at most 18 carbon atoms, a lower alkenyl group having preferably 1 to 4 carbon atoms or a cyclohexyl radical, unsubstituted or substituted by lower alkyl groups having preferably 1 to 4 carbon atoms. Fiber materials dyed with these dyestuffs exhibit very good fastness properties, especially fastness to wet processing, rubbing and dry-cleaning.

United States Patent [191 Seiler et al.

[ MONO OR DISAZO DYESTUFFS CONTAINING A DIAMINO, HALOTRIAZINYL ORPYRIMIDINYL SUBSTITUENT [75] Inventors: Herbert Seiler, Riehen; PaulDussy,

Basel, both of Switzerland [30] Foreign Application Priority Data Feb.26, l969 Switzerland 2862/69 July 7, 1969 Switzerland 1031 1/69 [52} US.Cl. 260/153, 8/41 B, 260/146 D,

[51] Int. Cl.... C09b 62/08, C09b 62/24, D06p 1/38 [58] Field of Search260/153, 154, 249, 249.8,

Primary ExaminerFloyd D. Higel Attorney, Agent, or Firm-Wenderoth, Lindand Ponack [.451 Oct. 22, 1974 [5 7] ABSTRACT Valuable reactivedyestuffs containing no acid, saltforming, water-solubilizing groups andwhich, among others, can be applied to hydrophobic fibers especiallypolyamide fibers from organic solvents, especially aprotic solventscorrespond to the formula wherein D represents the radical of an organicdyestuff, Q represents the bridging member NX,,-, -O-, -S- or -NX;,CO-,whereby X denotes hydrogen or a lower alkyl group, R represents theradical of a nitro gen heterocycle containing at least one substitutentwhich can be split ofi as anion and which is bound to a ring carbon atomadjacent to a tertiary nitrogen atom, X, represents hydrogen, an alkylor an alkoxyalkyl group and X represents an alkyl or an alkoxyalkylgroup having in all at least 4 carbon atoms, whereby X, and X musttogether contain, when X, denotes an alkyl or an alkoxyalkyl group, atleast 8 carbon atoms, or X, represents a cyclohexyl radical,unsubstituted or substituted by lower alkyl groups having preferably 1to 4 carbon atoms, and X. represents an unsubstituted or substitutedalkyl group having at most 18 carbon atoms, a lower alkenyl group havingpreferably 1 to 4 carbon atoms or a cyclohexyl radical, unsubstituted orsubstituted by lower alkyl groups having preferably 1 to 4 carbon atoms.Fiber materials dyed with these dyestuffs exhibit very good fastnessproperties, especially fastness to wet processing, rubbing anddrycleaning.

9 Claims, No Drawings MONO OR DISAZO DYESTUFFS CONTAINING A DlAMlNO,HALOTRIAZINYL OR PYRIMIDINYL SUBSTITUENT DETAILED DISCLOSURE Drepresents the radical of an organic dyestuff,

represents the bridging member NX O-, S- or --NX CO, whereby X denoteshydr gen or a lower alkyl group,

R represents the radical of a nitrogen heterocycle containing at leastone substituent which can be split off as anion and which is bound to aring carbon atom adjacent to a tertiary nitrogen atom,

2 wherein D has the mea'ninggiven under Formula I and 0 represents NHXOH or SH, whereby X denotes hydrogen or a lower alkyl group, to give adyestuff of Formula lV,

D-Q-R' wherein D, Q and R have the meaning given under Formulae l andll,

X represents hydrogen, an alkyl or an alkoxyalkyl group and X representsan alkyl or an alkoxyalkyl group having in all at least 4 carbon atoms,whereby X, and X must together contain, when X denotes an alkyl or analkoxyalkyl group, at least 8 carbon atoms,

X, represents a cyclohexyl radical, unsubstituted or substituted bylower alkyl groups having preferably 1 to 4 carbon atoms, and

X represents an unsubstituted or substituted alkyl group having at most18 carbon atoms, a lower alkenyl group having preferably 1 to 4 carbonatoms or a cyclohexyl radical, unsubstituted or substituted by loweralkyl groups having preferably 1 to 4 carbon atoms. The new, valuable,waterinsoluble reactive dyestuffs of Formula l are obtained by reactinga compound of Formula ll,

Hal (C0) R (ll) wherein R represents the radical of a nitrogen,heterocycle containing at least two substituents which can be split offas anion,

n represents 1 or 2 and Hal represents chlorine, bromine or fluorine,with an organic dyestuff of Formula lll,

and subsequently reacting the obtained reaction product with an amine ofFormula V,

wherein X and X have the meaning given under Formula I, and therebyselecting the components so that the obtained reactive dyestuff containsno acid, salt-forming, water-solubilizing groups.

A modification of the process according to the invention, for theproduction of reactive dyestuffs of Formula I, wherein 0 represents thebridging member -NX 00r-s-, whereby X denotes hydrogen or a lower alkylgroup, and for D, R, X1 and X that applies which is stated under Formula1, consists in reacting a compound of Formula II, wherein n representsone, and for Hal and R that applies which is stated above, firstly withan amine of the above mentioned Formula V to give a compound of FormulaVl,

. Hal-RN wherein Hal, R, X, and X have the above given meaning, andsubsequently reacting the compound of Formula Vl with a dyestuff ofFormula lll.-

The radical of an organic dyestuff D can belong to any desired classesof dyestuffs. The classes of dyestuffs, however, which are primarily tobe considered in this case are those which are technically easilyaccessible. For this reason, D represents in Formula 1, eg the radicalcontaining no acid, salt-forming, watersolubilizing groups of a nitro,acridone, methine, perinone, peridinecarboxylic acid imide,quinophthalone, naphthoquinonimine dyestuff, or the radical of ametalfree or heavy metal-containing phthalocyanine dyestuff and, inparticular, the radical of a mono or disazo dyestuff, optionallycontainingheavy metal, or of an anthraquinone dyestuff.

These radicals of organic dyestuffs can contain substituents common indyestuffs, which substituents do not dissociate anionically, e.g.,halogen atoms such as fluorine, chlorine or bromine; cyano or nitrogroups; hydrocarbon groups, especially lower alkyl groups such asmethyl, ethyl, isopropyl, tert.butyl, amyl, and lower alkenyl groups;substituted lower alkyl or alkenyl groups, eg perfluoro-(lower) alkylgroups such as trifluororriethyl, also hydroxyalkyi groups, e.g.,hydroxy- (lower) alkyl such as hydroxyethyl or -y-hydroxypropyl;

cyanoethyl or B, ,B-dicyanovinyl; ether groups, preferamember -NX and Xrepresents hydrogen,

' erably from 4 to 18, more particularly bly lower alkoxy groups, butalso aryloxy groups such as methoxy, ethoxy, butoxy, phenoxy,methylphenoxy; thioether groups, e.g. lower alkylthio or phenylthiogroups such as methylthio, ethylthio, phenylthio; acyl groups such aslower alltanoyl, aroyl, lower alkylsulphonyl or arylsulphonyl groups;arylsulphonyloxy groups such as phenylsulphonyloxy groups; primary,secondary or tertiary amino groups; acylamide groups, especially loweralkanoylamide groups such as acetylamide; lower alkoxycarbonylamidegroups such as ethoxycarbonylamide, or aroylamide groups such as'benzoylamide groups; lo'wer' alkylsulphonylamide or arylsulphonylamidegroups; carboxylic acid amide and sulphonic acid amide groups,optionally monoor disubstituted at the nitrogen atom, especiallyN-loweralkyl? or N,N-di-lower-alkylsulphonic acid amide groups.

In Formula I, preferably presents the bridging ethyl or propyl. I

As radical of a nitrogen heterocycle, R represents, in particular, atriazinyl or diazinyl radical, including quinoxaline, phthalazine,quinazoline and pyridazine radical containing as substituent which canbesplit off as anion, e.g. lower alkylsulphonyl or dinitrophenoxy groups,particularly, however, halogen atoms such as chlorine, bromine orfluorine.

X in the meaning of an alkyl or alkoxyalkyl group particularly denotessuch groups having from 1 to 18 carbon atoms; if both X, and X representan alkyl or alkoxyalkyl group, then each of these groups has preffrom 8to 18 carbon atoms.

As a cyclohexyl radical, optionally substituted by lower alkyl groups, Xand X represent, e.g. the lor 4-methylcyclohexyl radical, especially,however, the unsubstituted cyclohexyl radical. lf X denotes anoptionally substituted alkyl radical or an alkenyl radical,

then this. radical can be both straight-chained and branched. if thealkyl radical X is substituted, then suitable substituents are, inparticular, hydroxyhlower alkoxy, lower alkenyloxy and cyano groups.Examples of optionally substituted alkyl groups, denoted by X are:methyl, ethyl, Z-hydroxyethyl, isopropyl, sec. butyl, hexyl, octyl,dodecyl, tetradecyl, octadecyl, 2- ethylhexyl, 2-methoxyethyl,Z-ethoxyethyl, 2,2- diethoxyethyl, 2,2-dibutoxyethyl, 2-vinyloxyethyl or2-cyanoethyl. Examples for X as an alkenyl group are the vinyl and allylradical.

ln preferred compounds of Formula I, X represents, when X, denoteshydrogen, particularly an alkyl group having 8 to 18 carbon atoms; if X,and X each represent an alkyl group, then together these preferablycon-.

tain 8 to 36 carbon atoms.

In particularly preferred compounds of Formula I, however, X representsthe unsubstituted-cyclohexyl radical and X, represents an unsubstitutedalkyl radical having 1 to 4 carbon atoms, especially the methyl or ethylradical. These preferred compounds are distinguished by their good toexcellent solubility in organic zines having at least three labilehalogen atoms, e.g. cyanuric chloride, cyanuric bromide, 2,4,6-trichloropyrimidine or 2,4,6-trifluoro-pyrimidine,

2,4,6-tribromoor 2,4-difluoro-o-chloro-pyrimidine.

The trihalogenpyrimidine can optionally carry in the 5-position, e.g.the following substituents: chlorine, bromine, cyano, the nitro group,carboxylic acid amide or sulphonic acid amide groups, optionallysubstituted at the nitrogen atom, carboxylic acid methyl ester or ethylester groups; acyl, e.g. benzoyl; alkenyl, e.g. allyl, chlorovinyl,chloroor bromo-methyl. Examples of such further substitutedtrihalogenpyrimidines are: 2,- 4,5,6-tetrachloropyrimidine, 5bromo-,5-cyano-, 5- nitro-, 5-chloromethyl-2,4,6-trichloroor-trifluoropyrimidine, particularly 5-chloro-2,4,6-trifluoropyrimidine.

Also suitable are dihalogenpyrimidinecarboxylic acid halides,2,3-dihalogenquinoxalinecarboxylic acid ha lides,l,4-dihalogenphthalazinecarboxylic acid halides or2,4-dihalogenquinazolinecarboxylic acid halides such as, e.g. thecarboxylic acid halides of the 2,4- dibrom0-, 2,4-difluoroor, inparticular, 2,4- dichloropyrimidine-S- or -6-carboxylic acid, 2,4-dichloro-6-chloromethyl-pyrimidine-S-carboxylic acid, 2,3or2,3-dichloro-quinoxaline-o-carboxylic acid, 1,4- difluoro-,1,4-dichloroor l,4-dibromophthalazine-6- carboxylic acid,2,4-dichloro-quinazoline-6- or -7- carboxylic acid or2,4-dichloropyrimidyl-5-acetic acid.

Further compounds of Formula ll are: tetrachloropyridazine-,trichloro-l,2,4-triazineand 3,6- dichloropyridazine-S-carboxylic acidchloride.

Compounds of Formula ll are preferred, wherein Hal represents chlorine,n represents one and R represents a triazinyl radical having two labilehalogen atoms, especially cyanuric chloride; compounds of Formula ll,wherein Hal represents chlorine or fluorine, n represents one and Rrepresents a diazinyl radical having at least two labile halogen atoms,especially 2,45,6- tetrachloropyrimidine,5-chIoro-2,4,6-trifluoropyrimidine or 2,4,6-trifluoropyrimidine, orcompounds of Formula ll, wherein Hal represents chlorine, n representsone and R represents a diazinyl radical having at least two labilehalogen atoms, especially 2,4- dichloropyrimidine-S- or -6-carboxylicacid.

Examples of amines of Formula V, usable in the process according to theinvention are: isobutylamine, tert- .butylamine, isohexylamine,heptylamine, tert.octylamine, nonylamine, decylamine, undecylamine,tetradecylamine, hexadecylamine, heptadecylamine, octadecylamine anddodecylamine, N-ethyl-N- octadecylamine, N-methyl-N-dodecylamine,dibutylamine, dipentylamine, dihexylamine, dioctylamine, didodecylamine,Z-methoityethylamine, 2- ethoxyethylamine,3-methoxy-2-methyl-propylamine, 3-(Z-ethylhexoxy)-propylamine,methoxyhexylamine, 3-methoxybutylamine, N,N-diethoxyethylamine,N,N-dibutoxyethylamine, N-methyl-, N-ethyl-, N-propyl-, N-tert.butyl-,N-isoamyl-, N-hexyl- N-heptyl-, N-nonyl-, N-dodecyl-, N-hexadecyl-, N-

octadecyl-, N-oleyl-, N-(2-ethylhexyl)-, N-(Z- hydroxyethyl N-(B-hydroxypropyl N-( 2- methoxyethyl)-, N-(2-ethoxyethyl)-, N-(2-cyanoethyl)-, N-(2,2-diethoxyethyl)-, N-(2,2-dibutoxyethyl)-,N-(3,3-dimethoxypropyl), N-(2- vinyloxyethyl)-, N-vinylorN-allylcyclohexylamine, 1-cyclohexylamino-2-propanol, dicyclohexylamine,

5 N- l -dimethylcyclohexylamine, N-isopropyl- 1 -methylcyclohexylamineand N-4-dimethylcyclohexylamine.

For the reaction of a compound of Formula II with a dyestuff of FormulaIll and of the obtained reaction product of Formula IV with an amine ofFormula V. using the process according to the invention, as well as forthe reaction of a compound of Formula II, wherein n represents one, withan amine of Formula V and of the obtained compound of Formula V1 with adyestuff of Formula Ill, using the modified process according to theinvention, the conditions have to be chosen so that a premature exchangeof labile substituents does not occur either as a result of too high apH-value of the reaction medium or in consequence of too high atemperature. The reaction is performed by methods known per se, e.g. inaqueous suspension, advantageously, however, in an organic solvent, e.g.in an organic solvent which is inert to the reactants, such as acetone,dioxane, methylethyl ketone, ethyl glycol monomethyl ether or -ethylether, or in a mixture of such a solvent with water. The reaction iscarried out preferably at low temperatures, whereby the choice of thesuitable temperature depends principally'on the lability of thesubstituent which can be split off as anion, of the starting materialsused. Advantageously, temperatures between and 80C are used.

In order to neutralize the hydrogen halide being released during thereaction, it is possible to add to the reaction mixture, acid-bindingagents such as sodium carbonate, sodium bicarbonate, potassiumphosphate, alkali salts of lower fatty acids, e.g. sodium or potassiumacetate, ammonium acetate or an excess of the amine of Formula V.

If the reaction is performed in a mixture of an inert organic solventwith water, than it is advantageous to operate at a pH-value between 5and 9, whereby the pH-value during the reaction is maintained constantby addition of one of the stated acid-binding agents.

The isolation of the dyestuffs, obtainable according to the invention,is performed in the usual manner, e.g. by filtration, concentration ofthe solvent and filtration, removal by distillation of the solcent andfiltration or precipitation from the solvent and filtration.

The drying of the dyestuffs, obtainable according to the invention, isadvantageously carried out under mild conditions, i.e., at a moderatelyelevated temperature and preferably in vacuo.

The reactive dyestuffs of Formula I, which can be produced according tothe invention, are suitable for the dyeing and printing of organicmaterial of very diverse kinds, by methods known per se. Suitable asorganic material are, in particular, hydrophobic fibres such as fibrematerial made from linear high-molecular esters of aromaticpolycarboxylic acids with polyfunctional alcohols, such as polyethyleneglycol terephthalate, cellulose-diand -tri-acetate fibres, polyvinylfibres and, in particular, synethetic polyamide fibres.

A particular advantage of the reactive dyestuffs, obtainable accordingto the invention, is that they are excellently suitable for applicationfrom aprotic solvents alone, or from a solvent mixture consisting ofaprotic solvent and a liquid, water-soluble, organic solvent which boilsbelow 220C.

Thereby even and deeply coloured dyeings are obtained on the statedfibre material which, without an alkaline aftertreatment, have very goodfastness properties, especially fastness to wet processing, rubbing anddry-cleaning.

Compared to known comparable reactive dyestuffs which contain noalkylamino or alkoxyalkylamino group on the reactive radical or whichcontain a lowermolecular alkylamino group ot the cyclohexylamino groupon said radical, the reactive dyestuffs of Formula I, obtainableaccording to the invention, are characterised by an appreciably bettersolubility in an aprotic solvent alone, or in a solvent mixture, e.g. ina solvent mixture consisting of lower aliphatic halogenatedhydrocarbons, such as trior tetrachloroethylene (perchloroethylene), anda liquid, water-soluble or watermiscible organic solvent boiling below220C, such as lower alkanols or N,N-dialkylamides of lowermonocarboxylic acids. Thereby deeply coloured and fast dyeings areobtained.

The following Examples illustrate the invention. In the Examples, thetemperatures are given in degrees Centigrade.

Example 1 N( a 1r)2 24 g of 4-dimethylamino-4'-amine-l,l-azobenzene aredissolved neutral in 750 ml of acetone and 370 ml of water. To thesolution are added at 05, 22 g of 2,- 4-dichloropyrimidine-S-carboxylicacid chloride and the pH-value is maintained at 6 by the dropwiseaddition of sodium carbonate solution. After completion of thecondensation, the reaction mixture is heated to 3035, 24.1 g ofdioctylamine are added and the pH- value is held at 7 8, by thesubsequent dropwise addition of sodium hydroxide solution, untilcondensation is completed. The dyestuff of the above formula iscompletely precipitated by the addition of water, filtered off andwashed with water. After being dried in vacuo, the dyestuff is in theform of a yellow powder.

Example 2 NH-oo-fi-NHotHu N N If 24 g of4-dimethylamino-4'-amino-l,l-azobenzene are dissolved in 750 ml ofacetone and 370 ml of water. To this solution are added dropwise at O 5and at a pH-value of 6 7, 22 g of 2,4-dichloropyrimidine-6- carboxylicacid chloride in ml of acetone, and sodium carbonate solution issimultaneously added to maintain the pH-value. As soon as condensationis completed, 12.9 g of octylamine are added at 3035, at a pH-value of 78, and this is maintained at the given value by the subsequent dropwiseaddition of sodium hydroxide solution. After the reaction is completed,the dyestuff of the above formula is completely precipitated by theaddition of water, then filtered and washed with water. After drying ofthe dyestuff in vacuo, a yellow powder is obtained.

Example 3 22.7 g of 2-hydroxy-5-methyl-4-amino-l,l azobenzene aredissolved in 750 ml of acetone and 370 ml of water at a pH-value of 7.At 3035, a solution of 33.3 g of 2-dodecylamino-4,6-dichloro-1,3,5-triazine in 300 ml of acetone is then added and, by the simultaneousaddition of sodium carbonate solution, the pH-value is maintainedbetween 6 and 7. After completion of the condensation, the dyestuff ofthe above formula is completely precipitated by the addition of water,filtered and washed with water. The dyestuff, after being dried invacuo, is in the form of a yellow powder.

8 Example 4 or 0H A .N=N NH\ ,J-NHCsHi:

22.7 g of 2-hydroxy-5-methyl-4'-amino-l,l'-

azobenzene are dissolved in 750 ml of acetone and 370 ml of water at apl-l-value of 6.5 7. To this solution are added dropwise within 30minutes at 05, 18.4 g of cyanuric chloride dissolved in 100 ml ofacetone. An aqueous sodium carbonate solution is simultaneously addeddropwise in such a manner that the reaction remains always neutral.After completion of the condensation, the temperature is raised to 30with the simultaneous addition of, in all, 20.2 g of hexylamine, at apH-value of 7 8. After completion of the reaction, the dyestuff of theabove formula is completely precipitated by the yellow suspension beingpoured on to wa- 'ter. The dyestuff is then filtered and washed withwater.

After being dried in vacuo, it is in the form of a yellow powder.

Further dyestuffs are listed in the following Table l which can beproduced by the above described process. In the last column of thetable, the shades are given of the dyeings obtained with thecorresponding dyestuffs on polyamide-6.6 fabric.

TABLE I Example Shade on number Dyestufl polyamirlo-(Hi 5 CH3 N(C4H )zYellow,

s cm 01 Do. v N l N=N--NHO 0- N H NHCgHo 7 CH3 D0,

011 30112 01 CH fi H NH-CHzGH.

8 t H3 D0.

Q' i I i N HCaH1a 9 CH3 D0.

TABLE IContinued I O Ha Yellow.

azobenzene are dissolved in 800 ml of acetone and 400 ml of water andthe pH-value of the solution is adjusted I form of a yellow powder.

Example 64 22.7 g of 2-hydroxy-5-methyl-4'-amino-l ,l azobenzene aredissolved in 800 ml of acetone and 400 TABLE IContinued Sh d i r i iiiht Dyes tut! pol ya iriido-fifl 52 I v 0 1 i v No,

Nnl ,JNHcHzdHcmo OH:

Example 63 01 I OH O1 15 I OH N (11H;

- L 20 ml of water and the solution is adjusted to a pH-value H of 6 to7. To this solution are added dropwise in the Y I course of 30 minutesat O- S, 18.4 g of cyanuric chlog of 2'hydlioxy's'methyl4 'ammo'lilride, dissolved in 100 ml of acetone, and, simultaneously, an aqueous 2Nsodium hydroxide solution so that, in this way, the pH-value of thereaction solution always remains between 6 and 7. As soon as no furtheraminoazo dyestuff is detectable, l 1.3 g of N-methylcyclohexylamine areadded to the reaction mixture, the temperature is raised to 30-40 andthe pH-value of the solution kept between 6.5 and 7.5 by the occasionaladdition of 1N sodium hydroxide solution. After the reaction iscompleted, the dyestuff of the above formula is precipitated by thesuspension being poured on to water. The dyestuff is afterwards filteredand the suction-filter residue washed with water. After drying in vacuo,the dyestuff is in the form of a yellow powder.

In the following Table ll, further dyestuffs are listed which can beproduced by the above described process. In the last column of theTable, the shades of the dyeings are given which are obtained with thecorresponding dyestuffs on polyamide-6.6 fabric.

TABLE II Example Shade on number Dyestufl polyamide-6.G

0H ({31 Yellow.

66 CH3 D0.

cutout 01 H a it (linemen, a7 cr-r, m.

N..'-- (if \{-N=N -NI-I- N l 0 h N- l l if 33 Example l20 8 g of thedyestuff, produced according to Example 60, are dissolved in 1000 g oftrichloroethylene. With this solution a fabric made from polyamide-6.6is impregnated at room temperature, the fabric squeezed out to give adye liquor absorption of ca. 75 percent, relative to the dry weight ofthe material, and the impregnated material then dried at 80 in an airstream. The dyestuff is afterwards thermofixed during 5 minutes at 170.

Without aftertreatment, an even and well developed yellow dyeing isobtained having good fastness to wet processing and to rubbing.

If, instead of 1000 g of trichloroethylene, the same amount ofchlorobenzene is used, then likewise is obtained a deeply coloured, welldeveloped, yellow and fast dyeing.

Example l2! 8 g of the dyestuff, produced according to Example 64, aredissolved in 1000 g of trichloroethylene. A fabric made frompolyamide-6.6 is impregnated at room temperature with this solution. Thefabric is squeezed out to a dye liquor absorption of ca. 75 percent,relative to the dry weight of the material, and the impregnated materialis then dried at 80 in an air stream. The dyestuff is afterwardsthermofixed during 3 minutes at 170.

Without aftertreatment, an even and well developed yellow dyeing isobtained having good fastness to wet processing and to rubbing.

If, instead of the 1000 g of trichloroethylene, the same amount ofchlorobenzene is used, then likewise is obtained a deeply coloured, welldeveloped, fast, yellow dyeing.

What we claim is:

l. A reactive dyestuff, containing no acid, saltforming,water-solubilizing groups, of the formula wherein D represents theradical of a monazo or disazo dyestuff, unsubstituted or substitutedonly by halogen, cyano, nitro, lower alkyl, lower alkenyl, perfluoro(-lower)alkyl, hydroxy-(lower)alkyl, cyanoethyl, B, B-dicyanovinyl, loweralkoxy, phenoxy, methylphenoxy, lower alkylthio, phenylthio, loweralkanoyl, lower alkylsulphonyl, phenylsulfonyloxy, dimethylamino, amino,N-(B-cyanoethyhethylamino, diethylamino, methylethylamino,ethylbenzylamino, ethylbutylamino, N-(B-hydroxyethyl)ethylamino,,B-hydroxyethylamino, di(B- hydroxyethyl)amino, N-(B-cyanoethyl )-B-hydroxyethylamino, di(B-cyanoethyl)amino,

anilino, oxyanilino, methylamino, dimethylanilino,

methylanilino, lower alkanoylamide, lower alkoxycarbonylamide,benzoylamide, lower alkylsulphonylamide, N-loweralkylandN,N-diloweralkyllower alkylsulphonylamide, hydroxy or phenyl,

represents a bridging member NX,,, O,

S- or NX,,CO, whereby X, represents hydrogen or lower alkyl, representsdiazinyl or triazinyl containing only chlorine, bromine or fluorinesubstituents, each of which can be split off as anion and which is boundto a ring carbon atom adjacent to a tertiary nitrogen atom,

X & X represent the same or different alkyl or alkfrom 8 to 36 carbonatoms,

X, represents cyclohexyl or cyclohexyl substituted by lower alkyl, and

X, represents alkyl of l to 18 carbon atoms, alkyl of l to 18 carbonatoms substituted by a member selected from the group consisting ofhydroxyl, lower alkoxy, lower alkenyloxy and cyano, lower alkenyl,cyclohexyl or cyclohexyl substituted by lower alkyl.

2. A reactive dyestuff as claimed in claim 1, wherein Q represents the-NX,,- group, R represents triazinyl having one labile halogen atom ordiazinyl having at least one labile halogen atom, X, and X eachrepresent an alkyl group which together contain from 8 to 36 carbonatoms, or X, represents cyclohexyl and X represents an alkyl having from1 to 4 carbon atoms.

3. A reactive dyestuff as claimed in claim 1 wherein Q represents the NXCO- group, R represents diazinyl having at least one labile halogenatom, X, and X each represent an alkyl group which together contain from8 to 36 carbon atoms, or X, represents cyclohexyl and X represents alkylhaving from 1 to 4 carbon atoms.

4. A reactive dyestuff as claimed in claim 2 wherein 7. The reactivedyestuff as claimed in claim 1, which is of the formula 0 H N N al-In 8.The reactive dyestuff as claimed in claim 1, which is of the formulaCaHia Ha 9. The reactive dyestuff as claimed in claim I, which is of theformula UNITED STATES PATENT (EFFICE QERTIFICATE 0F CORRECTIQN Patent 3.843 ,624 Dated October 22, 1974 lnventofls) Herbert Seiler and PaulDussy It is certified that error appears in the above-identified patentand that said Letters Patent are hereby corrected as shown below:

In lines 21 and 22 of claim 1 (counting the formula as one line) change"and N,N-diloweralkyl-lower alkylsulphonylamide" to orN,N-diloweralkyl-sulphonylamide--.

In line 23 of claim 1 (counting the formula as one line) insert Q before"represents'h Rewrite lines 25 and 26 of claim 1 (counting the formulaas one line) as follows:

-drogen or lower alkyl,

R representsdiazinyl or triazinyl containing only chlorine, bromine orfluorine-.

Signed and Scaled this Twenty-eighth Day Of June 1977 {SEAL} Arrest:

RUTH C. MASON C. MARSHALL DANN Arresting Officer Commissioner nflarentsand Trademarks

1. A REACTIVE DYESTUFF, CONTAINING NO ACID, SALTFORMING,WATER-SOLUBILIZING GROUPS, OR THE FORMULA
 2. A reactive dyestuff asclaimed in claim 1, wherein Q represents the -NX3- group, R representstriazinyl having one labile halogen atom or diazinyl having at least onelabile halogen atom, X1 and X2 each represent an alkyl group whichtogether contain from 8 to 36 carbon atoms, or X1 represents cyclohexyland X2 represents an alkyl having from 1 to 4 carbon atoms.
 3. Areactive dyestuff as claimed in claim 1 wherein Q represents the -NX3CO-group, R represents diazinyl having at least one labile halogen atom, X1and X2 each represent an alkyl group which together contain from 8 to 36carbon atoms, or X1 represents cyclohexyl and X2 represents alkyl havingfrom 1 to 4 carbon atoms.
 4. A reactive dyestuff as claimed in claim 2wherein R represents chlorotriazinyl, 2,5-dichloropyrimidyl or2-fluoro-5-chloropyrimidyl.
 5. A reactive dyestuff as claimed in claim 3wherein R represents 2-chloropyrimidyl-5, or 2-chloropyrimidyl-6.
 6. Thereactive dyestuff as claimed in claim 1, which is of the formula
 7. Thereactive dyestuff as claimed in claim 1, which is of the formula
 8. Thereactive dyestuff as claimed in claim 1, which is of the formula
 9. Thereactive dyestuff as claimed in claim 1, which is of the formula